- USA
- Florida
- Anna Maria Island
- Holiday Homes
4630+ Anna Maria Island Holiday Rentals & Private Villas
- Sarasota
- ·
- Bradenton Beach
- 1.08 mi to center
10.0
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Private Pool -
Hot Tub -
Parking -
Pool
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Private Pool
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Hot Tub
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Parking
-
Pool
- Sarasota
- ·
- Holmes Beach
- 0.95 mi to center
9.0
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Parking
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Pool
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Balcony/Terrace -
View
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Parking
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Pool
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Balcony/Terrace
-
View
- Sarasota
- ·
- Anna Maria
- 0.18 mi to center
9.4
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Parking
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Ocean View -
Balcony/Terrace
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View
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Parking
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Ocean View
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Balcony/Terrace
-
View
- Sarasota
- ·
- Bradenton Beach
- 0.97 mi to center
10.0
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Parking
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Ocean View
-
Balcony/Terrace
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View
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Parking
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Ocean View
-
Balcony/Terrace
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View
- Sarasota
- ·
- Bradenton Beach
- 0.62 mi to center
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Internet -
Child Friendly -
Bedding/Linens -
Security/Safety
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Internet
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Child Friendly
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Bedding/Linens
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Security/Safety
- Sarasota
- ·
- Anna Maria
- 0.25 mi to center
10.0
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Private Pool
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Parking
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Pool
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Ocean View
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Private Pool
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Parking
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Pool
-
Ocean View
- Sarasota
- ·
- Holmes Beach
- 0.97 mi to center
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Parking
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Pool
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Air Conditioner -
Internet
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Parking
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Pool
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Air Conditioner
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Internet
- Sarasota
- ·
- Holmes Beach
- 0.83 mi to center
10.0
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Private Pool
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Parking
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Pool
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Ocean View
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Private Pool
-
Parking
-
Pool
-
Ocean View
- Sarasota
- ·
- Holmes Beach
- 0.95 mi to center
-
Parking
-
Pool
-
Balcony/Terrace
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View
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Parking
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Pool
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Balcony/Terrace
-
View
- Sarasota
- ·
- Holmes Beach
- 0.86 mi to center
10.0
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Private Pool
-
Hot Tub
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Parking
-
Pool
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Private Pool
-
Hot Tub
-
Parking
-
Pool
- Sarasota
- ·
- Holmes Beach
- 0.53 mi to center
9.8
-
Private Pool
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Parking
-
Pool
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Ocean View
-
Private Pool
-
Parking
-
Pool
-
Ocean View
- Sarasota
- ·
- Anna Maria
- 0.29 mi to center
9.8
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Private Pool
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Parking
-
Pool
-
Ocean View
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Private Pool
-
Parking
-
Pool
-
Ocean View
- Sarasota
- ·
- Anna Maria
- 0.31 mi to center
9.8
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
- Sarasota
- ·
- Anna Maria
- 0.32 mi to center
9.6
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Oceanfront -
Hot Tub
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Parking
-
Ocean View
-
Oceanfront
-
Hot Tub
-
Parking
-
Ocean View
- Sarasota
- ·
- Bradenton Beach
- 0.61 mi to center
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Oceanfront
-
Parking
-
Pool
-
Ocean View
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
- Sarasota
- ·
- Anna Maria
- 0.29 mi to center
10.0
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
- Sarasota
- ·
- Holmes Beach
- 0.28 mi to center
9.8
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
- Sarasota
- ·
- Holmes Beach
- 0.52 mi to center
9.6
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
- Sarasota
- ·
- Holmes Beach
- 0.32 mi to center
9.4
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
- Sarasota
- ·
- Bradenton Beach
- 0.41 mi to center
10.0
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Private Pool
-
Oceanfront
-
Hot Tub
-
Parking
-
Private Pool
-
Oceanfront
-
Hot Tub
-
Parking
- Sarasota
- ·
- Bradenton Beach
- 0.41 mi to center
9.8
-
Oceanfront
-
Hot Tub
-
Parking
-
Pool
-
Oceanfront
-
Hot Tub
-
Parking
-
Pool
- Sarasota
- ·
- Anna Maria
- 0.26 mi to center
9.6
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Private Pool
-
Hot Tub
-
Parking
-
Pool
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
- Sarasota
- ·
- Bradenton Beach
- 0.85 mi to center
10.0
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Private Pool
-
Hot Tub
-
Parking
-
Pool
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
- Sarasota
- ·
- Anna Maria
- 0.49 mi to center
10.0
-
Private Pool
-
Parking
-
Pool
-
Balcony/Terrace
-
Private Pool
-
Parking
-
Pool
-
Balcony/Terrace
About Anna Maria Island Holiday Homes on Rent Holiday
Discover more than 4630 holiday rentals in Anna Maria Island. Rent Holiday holiday homes has everything you need to find a place to stay near Anna Maria Island, FL.
Whether you are looking for luxury villas in Anna Maria Island, furnished homes, unique style condos, flats, cozy cottages for a romantic getaway, spacious apartment for family holidays, or stylish accommodation for a business trip, we can help you find the perfect place. Our holiday rentals include top amenities such as indoor/outdoor swimming pools, kitchen facilities, gyms, hot tubs, Internet connectivity, and more.
If you are planning to travel to Anna Maria Island with a whole family or group, Rent Holiday holiday accommodations make your trip memorable. We have plenty of places to stay in Anna Maria Island for families, large parties, or private owner accommodations for long or short trips. Anna Maria Island Pet-friendly holiday rentals are available. Book your favorite vacation rentals in Anna Maria Island with Rent Holiday. Rent Holiday makes it easy to compare and book holiday rentals today.
Frequently Asked Questions About Anna Maria Island Holiday Homes
What are the top rated Holiday Home Rentals in Anna Maria Island?
There are a lot of options in Anna Maria Island. If you plan on staying in the Anna Maria Island area, consider making a reservation for a few nights at one of these properties as these have been rated the top Holiday Home Rentals in Anna Maria Island:
- Best Little Beach House on Anna Maria Island! With a pool & steps to the beach!
- Beautiful, Gulf-Front Home on Bean Point-Halcyon House
- Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!
- AMI Sunset Beach Gulf View Retreat w/Pool + Decks + WiFi + Dog-friendly
- 2 Bedroom/2 Bath Ground Level With a Heated Pool
- Dragonfly - Southern charm on the North end of Anna Maria Island
- 2nd House from the Beach with No Roads to Cross
- Coastal Getaway Retreat –Steps to the Beach! 1BR/1BA. Sleeps 2. In 4-Plex. Pool
- Spectacular Beach & Dolphin Views! Huge Private Balcony! 2BR/2BA Upstairs Villa
- Spectacular Beachfront House with Pool
Which are the best holiday rentals in Anna Maria Island, FL?
There are many holiday rentals available in Anna Maria Island; however, here are a few of the most popular holiday homes listed in Anna Maria Island on our website:
What are the most family-friendly holiday homes in or near Anna Maria Island?
At Rentholiday most of our places to stay are perfect for families. Check out the complete list of holiday homes in Anna Maria Island to find one that works for you.
Can we get a self-catering family vacation rental in Anna Maria Island?
Yes, there are 4630 self-catering family homes and holiday rentals in Anna Maria Island.
What are the top luxury holiday homes near Anna Maria Island?
There are more than 4630 luxury holiday homes in or near Anna Maria Island, according to 2026 data from Rentholiday. Consider these homes for your next holiday:
